diff --git a/framework/core/locale/core.yml b/framework/core/locale/core.yml
index b842cd72b..c35d0964e 100644
--- a/framework/core/locale/core.yml
+++ b/framework/core/locale/core.yml
@@ -605,6 +605,7 @@ core:
 
     # These translations are displayed as error messages.
     error:
+      circular_dependencies_message: "Circular dependencies detected: {extensions}. Aborting. Please disable one of the extensions and try again."
       dependent_extensions_message: "Cannot disable {extension} until the following dependent extensions are disabled: {extensions}"
       extension_initialiation_failed_message: "{extension} failed to initialize, check the browser console for further information."
       generic_message: "Oops! Something went wrong. Please reload the page and try again."
diff --git a/framework/core/src/Extension/Exception/CircularDependenciesException.php b/framework/core/src/Extension/Exception/CircularDependenciesException.php
new file mode 100644
index 000000000..c2c052839
--- /dev/null
+++ b/framework/core/src/Extension/Exception/CircularDependenciesException.php
@@ -0,0 +1,25 @@
+<?php
+
+/*
+ * This file is part of Flarum.
+ *
+ * For detailed copyright and license information, please view the
+ * LICENSE file that was distributed with this source code.
+ */
+
+namespace Flarum\Extension\Exception;
+
+use Exception;
+use Flarum\Extension\ExtensionManager;
+
+class CircularDependenciesException extends Exception
+{
+    public $circular_dependencies;
+
+    public function __construct(array $circularDependencies)
+    {
+        $this->circular_dependencies = $circularDependencies;
+
+        parent::__construct('Circular dependencies detected: '.implode(', ', ExtensionManager::pluckTitles($circularDependencies)).' - aborting. Please fix this by disabling the extensions that are causing the circular dependencies.');
+    }
+}
diff --git a/framework/core/src/Extension/Exception/CircularDependenciesExceptionHandler.php b/framework/core/src/Extension/Exception/CircularDependenciesExceptionHandler.php
new file mode 100644
index 000000000..67e7cdf8d
--- /dev/null
+++ b/framework/core/src/Extension/Exception/CircularDependenciesExceptionHandler.php
@@ -0,0 +1,32 @@
+<?php
+
+/*
+ * This file is part of Flarum.
+ *
+ * For detailed copyright and license information, please view the
+ * LICENSE file that was distributed with this source code.
+ */
+
+namespace Flarum\Extension\Exception;
+
+use Flarum\Extension\ExtensionManager;
+use Flarum\Foundation\ErrorHandling\HandledError;
+
+class CircularDependenciesExceptionHandler
+{
+    public function handle(CircularDependenciesException $e): HandledError
+    {
+        return (new HandledError(
+            $e,
+            'circular_dependencies',
+            409
+        ))->withDetails($this->errorDetails($e));
+    }
+
+    protected function errorDetails(CircularDependenciesException $e): array
+    {
+        return [[
+            'extensions' => ExtensionManager::pluckTitles($e->circular_dependencies),
+        ]];
+    }
+}
diff --git a/framework/core/src/Extension/ExtensionManager.php b/framework/core/src/Extension/ExtensionManager.php
index 5e33db2bb..08d0be0ef 100644
--- a/framework/core/src/Extension/ExtensionManager.php
+++ b/framework/core/src/Extension/ExtensionManager.php
@@ -15,6 +15,7 @@ use Flarum\Extension\Event\Disabling;
 use Flarum\Extension\Event\Enabled;
 use Flarum\Extension\Event\Enabling;
 use Flarum\Extension\Event\Uninstalled;
+use Flarum\Extension\Exception\CircularDependenciesException;
 use Flarum\Foundation\Paths;
 use Flarum\Settings\SettingsRepositoryInterface;
 use Illuminate\Contracts\Container\Container;
@@ -157,6 +158,13 @@ class ExtensionManager
         return $this->extensions;
     }
 
+    public function getExtensionsById(array $ids): Collection
+    {
+        return $this->getExtensions()->filter(function (Extension $extension) use ($ids) {
+            return in_array($extension->getId(), $ids);
+        });
+    }
+
     /**
      * Loads an Extension with all information.
      *
@@ -397,10 +405,19 @@ class ExtensionManager
      * Persist the currently enabled extensions.
      *
      * @param array $enabledExtensions
+     * @throws CircularDependenciesException
      */
     protected function setEnabledExtensions(array $enabledExtensions)
     {
-        $sortedEnabled = static::resolveExtensionOrder($enabledExtensions)['valid'];
+        $resolved = static::resolveExtensionOrder($enabledExtensions);
+
+        if (! empty($resolved['circularDependencies'])) {
+            throw new Exception\CircularDependenciesException(
+                $this->getExtensionsById($resolved['circularDependencies'])->values()->all()
+            );
+        }
+
+        $sortedEnabled = $resolved['valid'];
 
         $sortedEnabledIds = array_map(function (Extension $extension) {
             return $extension->getId();
diff --git a/framework/core/src/Foundation/ErrorServiceProvider.php b/framework/core/src/Foundation/ErrorServiceProvider.php
index 495303b61..7e9d63d41 100644
--- a/framework/core/src/Foundation/ErrorServiceProvider.php
+++ b/framework/core/src/Foundation/ErrorServiceProvider.php
@@ -58,6 +58,7 @@ class ErrorServiceProvider extends AbstractServiceProvider
             return [
                 IlluminateValidationException::class => Handling\ExceptionHandler\IlluminateValidationExceptionHandler::class,
                 ValidationException::class => Handling\ExceptionHandler\ValidationExceptionHandler::class,
+                ExtensionException\CircularDependenciesException::class => ExtensionException\CircularDependenciesExceptionHandler::class,
                 ExtensionException\DependentExtensionsException::class => ExtensionException\DependentExtensionsExceptionHandler::class,
                 ExtensionException\MissingDependenciesException::class => ExtensionException\MissingDependenciesExceptionHandler::class,
             ];